When to Jump

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Life is short. How do you know you're living it to its full potential? When do you stay put? And when do you change things up? When to Jump is dedicated to exploring the fundamental question we all think about: When do you chase your dreams? Hosted by Mike Lewis, who left his comfortable job in finance to become a professional squash player, and featuring inspiring conversations with all sorts of "jumpers"--from entrepreneurs and athletes to artists and side hustlers.

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Recent Reviews
  • blossoms
    Great concept
    I have only listened to one episode, but the concept is tremendous. Very few people succeeds by staying in one job or doing one thing, so jump must be necessary to the success of many. But giving up what one already have, which is the other side to jump, is difficult. That’s why this show could be a good idea. Looking at how other people have done it. Thanks
  • blue234154
    Not as good
    Just listen to How I Built This. A much better version of a podcast like this
  • Bronx161Street
    The New Format...
    Lazy. We want a conversation not a produced single voice.
  • jconoley writes
    A great resource
    The funny thing about making a jump is once you do it everyone asks you “how did you do it?” I’m so grateful for this podcast because now I have a resource to refer others to after I tell them my own story. I love how mindset issues & logistics are both covered in the interviews. Mike is an engaging interviewer who gets to the questions his audience is most interested in. Thank you for all your hard work!
  • ElenaD123
    ♥️from a jumper who helps women lawyers jump!
    I love “went to jump” and recommend it to my clients and anyone who will listen! Mike has such a beautiful and empathetic interviewing style. It’s so not about him, and he elicits the jumper’s stories with beauty and ease. As someone who has made a few jumps, and now helps women lawyers who feel stuck and unhappy make their own jumps, I know the value of sharing stories. I love the quote I heard Mike say in an episode: “To live an interesting life, be interesting!” YES! Thank you for doing this. - Elena Deutsch
  • Kimgjolly
    Great podcast, and referral to other great podcasts
    I’ve been listening for a month on the way to work, and have heard some inspiring stories and great advice. Also, this podcast led me to several other resources that are helpful as well (Gretchen Rubin, Julie Morgenstern, Julie Finn) and hopefully one day I will get my jump together. Until then, I am glad to hear positive stories from the world!
  • J. Barshop
    Insightful, actionable and compelling - highly recommend!
    Mike is absolutely phenomenal at expertly extracting those bits of gold listeners are looking for and he & his world-class guests consistently deliver for those craving compelling stories and actionable tips. Highly recommend listening and subscribing to When to Jump if you want the knowledge AND mindsets to become the very best version of yourself (and reach your overall goals as a result)!
  • Cece LA
    Inspiring & practical
    I learned about When to Jump through another podcast Don’t Keep Your Day Job with Cathy Heller. This podcast resonates with me because of where I’m at in my life. Great speakers, inspiring stories, practical wisdom. I bought Mike’s book too! I think one day I’ll be a guest on his show ;) Keep up the great work! Thank you for all you do! Voting for Los Angeles to host the next When to Jump main event :)
  • Sadye Evyn
    Inspiring + authentic
    As a creative who’s currently stuck in a non-creative and very corporate job and eager to make a change, I’m so glad I came across When to Jump. I’ve only listened to one episode so far, but I’m hooked and excited to add this show to my arsenal of inspiration for leading a creative life and letting go of the fear that’s been holding me back for years. Thank you, Mike, for starting this and for writing your book–can’t wait to read it!!
  • bethandtaber
    Great stories
    I appreciate the range of experience that Mike is able to collect and the stories that each have to share
  • MJ_45
    Inspiration
    I love this podcast! It's really a great way to hear about what "jumps" others made and what the outcome was. Not only does it encourage me to continue chasing my dreams, but is also inspires new ideas and what others have done to accomplsh similar goals.
  • jcc1679
    highlight of my week
    Ever heard that Marianne Williamson quote that goes along the lines of being the most authentic version of you, gives others permission to do the same? Sometimes we all need a little comfort that we are not alone in our desire to "jump" - listen in for inspiration.
  • Mafilinda9
    Great idea!
    Thanks for creating this! We needed it!
  • AndyCabis
    I have been waiting for this podcast!
    When to Jump is filled with amazing courageous stories of people who decided to follow their heart and not settle for the normal or for average. I’m so glad this podcast exists. I have been waiting for raw and authentic content like this for a long time!
  • booitsbecky
    great show!
    as a "jumper" myself, this show is great!
  • 50 and going
    Jumping
    As a Mother Of 4 remarkable children.The oldest 24 youngest 7 lol . I am 46 and currently jumping with knees knocking.. and 1 eye open. Scared as hell, helping financially it will all come together. I am ever so grateful for Beautiful people giving wonderful words of wisdom. Thank you! I hope you and this PODCAST go far ..
  • A1501ms
    Love this
    Similarly to How I Built This or Masters of Scale, this show is fine storytelling at its best with interesting guests and a great host. Can’t wait to hear more stories in the coming weeks!
  • jessratcliffe
    Packed with inspiration!
    The When to Jump podcast is one you want to subscribe to immediately. I listened to the first two episodes back-to-back and I can’t wait for the third! The sign of a great podcast: when it keeps you on the treadmill for an extra 10 minutes so you can finish the episode!
  • geeksharka
    Learning to Jump
    As everyone knows, wanting to jump and actually jumping, are two very different things. This podcast nicely captures the background thoughts of guests whom have made jumps in their lives, both large and small. Interesting and encouraging for those of us who may feel there's more out there to explore, and want to know how to get there.
  • jeannie_vaughan
    Inspiration and Authentic
    The stories shared on the When to Jump podcast are authentic and inspiring. Mike features stories from successful leaders who did not have everything figured out when they made the jump. HIGHLY recommend this if you’re looking for inspiration!
  • DamonPB
    Jumper
    Really enjoyed this first episode. Sheryl Sandburg is so inspiring. I left my job in the tech industry to build a squash club where hardly anyone has heard of squash. I’m still questioning whether I should have jumped. I just don’t know what else I would be doing though.
  • Charlotte CM
    Inspiring & Real
    A lovely podcast for a swift kick in the pants! Let’s get jumping, y’all!
  • LPColella
    When to Jump Inspires
    I’ve been following When to Jump since the early stages, and it’s been amazing to see how it’s evolved. It’s so important for people to realize they can be anything they want to be and do anything they want to do if they’re willing to try. When to Jump does that for you - it will inspire you to follow your dreams, whatever those may be.
  • Happy shopper in Boston
    Inspiring
    Interesting stories told by even more interesting people, amazing podcast
  • sjg326
    Honest and Engaging
    I’m hooked already! The stories drew me in and I’m yearning for more.
  • Vlurie
    Great inspiring message
    Loved your first podcast with Sheryl Sandburg. Great insight to believe in yourself and know when to jump. Thank you.
  • Jackson Slavik
    Inspiring
    Incredibly inspiring stuff!
  • bob657698
    Inspiring and Thought Provoking
    Awesome podcast - just listened to the premiere episode with Sheryl Sandberg. Very open conversation about her transition from government to tech and the thought process that she went through. Challenges you to think about if/when it is time to let go of the hold to start something new If you’re considering making a jump I encourage you to listen to the pod for some inspiration and confidence. “Long term dream and short term plan. Enjoy the process.”
  • RefundKing
    Great Stories
    Love these stories on Huff Post. Can't wait for the podcast and the book!
  • balemos
    As real as it gets
    Mike and When to Jump is about the truth of being human. We are all called to jump Into our purpose. This podcast brilliantly explains why and how. Mike is the man, the stories are powerful, and it all helped me jump too.
  • Brunchton
    Authentic
    Mike's story is amazing. Can't wait for his podcast
  • Duggan7
    Permission to jump!!
    Mike’s jump from safe to the unknown is incredible. Can’t wait to hear more jump stories.
  • Thalsted90
    Honest & Authentic
    Not revisionist history, but rather a walk through the arc as it happened. A remarkable pod by an even more remarkable man.
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